


Feathers rhymes with Leathers

by Notsalony



Category: Supernatural
Genre: Anal, Backstory, Bitch!dean, Bondage, Cuffs, Destiel - Freeform, Dom!Cass, Electo, Electricity, Kinktober, M/M, Other, Restraints, Sub!Dean, Suspension, Time Manipulation, Top!Cass, bottom!Dean, e-stem
Language: English
Status: Completed
Published: 2021-01-05
Updated: 2021-01-05
Packaged: 2021-03-15 21:16:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,040
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28570632
Author URL: https://archiveofourown.org/users/Notsalony/pseuds/Notsalony
Summary: Dean has always had some kinks.  Nothing too extreme until after he came back from hell.  Getting a new body a few times back to back, and having met Chief has changed how he views some of his sexuality.
Relationships: Castiel/Dean Winchester
Kudos: 29





	Feathers rhymes with Leathers

**Author's Note:**

  * For [master_necrosis](https://archiveofourown.org/users/master_necrosis/gifts).



> This was written as a Kinktober gift for Rose.

Despite what the various supernatural creatures that had taken a bite out of him would tell you, Dean Winchester had taste. Several tastes.

Big titted asian beauties. Big titted beauties. And maybe just a hint of none vanilla sex. I mean, honestly, who in their right mind hunts the monsters and the stuff that goes bump in the night but likes it plain jane missionary style every night? No one that isn’t going to get a bullet between their eyes sooner or later, either by a monster, a demon, a hunter or themselves.

It started for him when he was on an early case. He might have been nineteen, almost twenty when this board house wife needed pumped for information. He didn’t realize that the way she liked to _pump_ for _anything_ was with sweet young men like him naked and tied to the roof of her bed while she did unspeakable things to them.

Unspeakable because when his dad had asked him about it in the morning he’d turned crimson and rubbed his own ass out of the memory and his dad had laughed. Told him not to speak of it again and so he hadn’t. Ever. Not when he started sleeping around, not when he talked with other hunters. Not when anything.

Granted when ever they got a case where there was someone who swung a little… _aggressive_ towards the bondage and non-vanilla crowd, his dad had steered them towards him. Did his dad know that he was whoring his son’s ass out to women for information? A few of them didn’t even have anything to do with the case and he started to wonder if his dad just assumed he liked this sort of thing.

Maybe he did.

He’d happened to find a hole in the wall gas station that catered to some perverse and varied interests in their magazine selection, and in one of them it’d been all about submissive men and the women that used them. Dean had blushed and bought it, and later about died when his dad caught him jerking it to a spread that had a guy built like him being taken by two chicks with massive dildos. He’d likely have lived that down eventually if his dad hadn’t went missing on a hunt some time after that and then started his obsessive search for his father and his brother.

Sammy teased him once in a while. And sure he over compensated by leaving a lot of lesbian porn and anime out where Sam could see it. All the while hiding all the massive amounts of bondage porn he was collecting and squirreling away. Really no one knew a thing about his sex life right up to the point he died and went to hell.

Then he was chained up for decades, tortured and raped till he broke and started doing the same to other _innocent_ souls. He’d taken great pleasure in being the dom and the top while he was in hell. He looked forward to being the one to hurt others and extract their secrets as his day to day work in hell, and then he woke up.

Clawing his way out of his own grave, and spitting up dirt he’d come back to life and been more and more broken as he struggled to put his life together. Eventually they met Cass and found out he’d lead the group that pulled Dean from Hell.

It was like a gnawing hunger inside him.

Clawing at his insides till he eventually started looking for someone to scratch. He started looking for any one who could make him feel that. Sometimes the women left before the night was over. And more than once it was suggested that with his _tastes_ he’d be better off finding men who were more into pain or _that_ sort of thing. And he’d thought about it a time or two. Even had some guys hit on him and gotten a little rough and got his engine revved up only for them to back up.

That was worse. And he’d have to spend so much time pounding his flesh till he found an unsatisfied end that left him feeling empty inside. Which was why when they took a case in Vegas and he ended up in a dungeon and at the hands of Chief.

Chief put him in his place. Put him in a sub space that he hadn’t reached since he was nineteen and at the mercy of that house wife. He’d made a couple extra trips, even going to the point of asking Cass to teleport him back there several times to strip off and chain his hands up. Used and abused by Chief and anyone he brought in till eventually there was a schedule conflict and Chief wasn’t available.

He’d gotten sloppy. Too complacent. He didn’t have a backup plan.

That’s when Cass found him in a jail cell having picked a fight to at least have the cold feel of cuffs on his wrists tonight. Cass had stood there watching him for a while before he put the guards to sleep so he could speak to Dean without being over heard.

“Dean.”

“Cass… I’ll call you when I need a ride.”

“You’re in jail.”

“Yes I am. Goodbye.”

“Why are you in jail?”

“You remember the pizza boy movie you watched?” Dean didn’t think he’d ever get the image of Cass stumbling across porn for the first time out of his head. He’d watched a pizza boy bang some faceless chick in a cheesy porn flick. Hell he’d used it to teach himself how to have sex. Something that Dean still couldn’t wrap his head around.

“You attempted to solicit a pizza boy for your night time meal?” Cass frowned.

“what… no. I was looking for sex but not that… _kind_ …” Dean sighed heavily.

“I don’t understand.”

“I meet a guy here in Vegas and let him tie me up and fuck me… okay Cass.”

“And you like being sodomized while chained up?” Cass frowned. “Because I’m pretty sure I’ve heard you say something to Samuel about…”

“That… that’s just a thing I say.” Dean blushed. “Sam doesn’t know.”

“I see…” Cass frowned, standing there in his trench coat that seemed to swallow him up. “And you’re in jail because?”

“He wasn’t available, and I needed the itch scratched and since no one else caters to that… _sorta thing_ here… at least no one that I know of… I sorta picked a fight so I’d at least end up in lock up for tonight.”

“Humans are strange creatures.”

“You don’t know the half of it.” Dean sighed. “But I suppose if you’re here you might as well get me out of these cuffs and take me home.”

“No.”

“I’m sorry, what?”

“You wished to be chained up. Correct?”

“Well yeah but…”

“While nude?”

“Generally yeah I like to be naked while I’m having sex…” Dean couldn’t follow the statement till a flash of light and he found himself completely naked with his hands cuffed behind his back. “Cass….” He heard his voice break and hated that more than anything just then.

“Do you feel better?”

“Cass what the hell are you doing?”

“Attempting to meet your needs.”

“What…?” Dean frowned and then slowly realized. “A-are you planning…”

“You did say you let the man who chained you up have sex with you.” Cass blinked into the cell. “Should I disrobe as well?”

“you don’t have to do that…” Dean tried to talk him off only to find his arms suddenly raise behind him as a chain formed to lift him up off the ground putting his ass more in line with Cass’ groin.

“There.”

“Castiel…”

“Dean, do you prefer lubrication?”

“YES!” Dean nodded hard, he didn’t care if he looked pathetic rocking back and forth chained up by his arms to the ceiling in the police station. He had cottoned on to the idea that not only was this happening but that Cass was taking things very VERY litteral.

“Okay.” Dean had a moment of wondering what the hell that meant when his legs went limp and the world seemed to fall sideways as he trembled hanging there. With out touching him, with out fingering him, Cass had massaged every muscle in his entire body to relax him before feeling his entire ass with about a gallon of lube. Dean was hanging there slack jawed, too relaxed and turned on to really process why Cass would think they needed that much lube.

“I’ll be gentle. This is my first time with a human.” He moved out of Dean’s line of sight, and Dean was reminded that Cass’ first time had been with a demon in a dead human’s body. What the fuck had they gotten up to that required this much lube…? Nope. No he did not want to think about that. He did… his mouth fell open as something touched his quivering hole.

“cass….” Dean nearly whispered.

“Thankfully my host is equipped with adequate appendages.” Apparently to a being who’s used to bosses who were the size of sky scrapers in their normal form and God, eleven hard inches was adequate.

To a mortal who’d never had anything larger than nine inches in him when he wasn’t in hell… Dean saw stars before Cass was even half way in him from the girth alone. But he didn’t stop till all of him was buried in to the hilt in Dean’s tight hole. Dean never thought of himself as tight. He’d been making these trips often enough that he had thought about buying a butt plug for the field because he was afraid he’d gotten too loose. But tight was the only way he could explain the feeling as Cass bottomed out in him and sat there for a moment before biting down on the back of Dean’s neck and wrapping his arms around him before a pounding so fast that at one point he was pretty sure that Cass would phase right through him or something equally ridiculous to that might happen.

But on and on for what felt like hours, Cass pounded away at Dean, only pausing when Dean would curse as his orgasm was wrenched from his untouched cock. Again and again his body milked as he was a passive part of his sex life, the even and regular sparks that seemed to come off of Cass’ cock stimulating his prostate and milking him from the inside out. A few dry orgasms and Dean nearly passed out as his body spasmed and twitched at the sensation, it reminded him a lot of the E-stim that Chief had. At some point he realized Cass was holding his balls and with shock as his mouth fell slack, he realized Cass was refilling his nuts with cum. This wasn’t going to be over with for some time.

At some point Dean saw the sun come up and felt for sure he was going to be free to recover and think about this whole situation. Only for the sun to set in reverse.

“I’m not stopping until you’re fully satisfied.” Cass reentered him to the hilt.

“fuck…”

“Clearly I’m not doing it right… you can still speak English.”

“what?”

“Meg said good sex ends when you can’t speak or one party starts talking Portuguese.”

“Cass I don’t speak Portuguese.”

“Neither did I till after the first time with Meg… but she told me I was quite good at it.” Cass began to change up his positions and Dean could feel his toes curling already.

Fuck…

“Besides, if this isn’t exactly what you want… you can always show me videos. Meg had quite the porn collection. And we only managed to get through the first room of it before you needed me.”

“f-first room…”

“Yes. There were a lot of interesting things in that first room. On an unrelated note… do you have any attraction towards bovine?” Dean’s eyes went wide at that and he started shaking his head no rapidly.

“soon as this is over… we’re talking safe words….” Dean sputtered as he clung to his restraints just trying to survive his nights of passion.

**Author's Note:**

> This story was written in front of a live studio audience.


End file.
